A Complete Beginner's Guide to Anal Sex

Raise high the butthole, carpenters. (If you are my parents, do not read this.)

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In 1977, Cat Stevens retired from music and underwent a dramatic conversion to become a religious Muslim named Yusuf Islam. I can totally relate to this now, because before I used to say I'd never have butt sex and then this weekend I had it.

A few years ago, I was so adamant about never having it that I had the following conversation with my then-roommate, Ben. Reality Bites, which I despise, was on TV.

"I really hate this movie more than anything in the world," I said.

"Even more than butt sex?" (We had discussed my terror of anal before.) "Like if you had to choose whether you were gonna watch Reality Bites or have anal sex—"

"I would rather have anal sex. The ranking is like, everything, and then anal sex, and then watching Reality Bites is dead last."

But that was when I was slightly younger, closed-minded, and very single — which allowed me to make sweeping generalizations about things I'd Never Do without being challenged on them. The risk/return ratio of anal sex seemed very lopsided (Return: The guy you're dating thinks you're cool, or whatever? Risk: Pooping on a penis.) But now that I'm someone's girlfriend, it turns out that when you really like someone, you're more willing to try things you never thought you'd try. Like watching Jason Statham movies and camping and losing the final and only virginity that you've retained since After-Prom.

1. Don't try it if you don't want to. There's a big difference between "I don't necessarily fantasize about getting a penis enema but I want to blow my partner's mind" and "I would rather die than do this but I guess I can suffer through it because he's been pressuring me." If you're in a mutually caring, healthy relationship (with a guy who goes down on you for half an hour, minimum), maybe you'll want to do it for your partner or you won't. Either way is 100 percent fine, and if he keeps pressuring you when you have made it clear that it is not on the table, tell him to suck it.

2. Even if you're monogamous, a condom is probably a good idea. It prevents bacteria from the bowels spreading anywhere. (I know, you really wanna fuck now.) Sexpert Dr. Emily Morse advises keeping baby wipes on the nightstand and to "never use the same condom going from vaginal to anal and back again." For obvious reasons/poopy vagina.

3. The right lube is twice as important as it is when having vaginal sex, which is already super-important. You might have heard that too much lube takes away the friction that makes it feel good for the dude. That's bullshit. There is no such thing as too much lube, because it makes it feel slightly less like you are using your butthole as a handbag for a flashlight.

4. Between thin water-based lubes (like Astroglide) and thicker ones (KY), go with the thicker ones, because they don't dry out as quickly. In sex educator Tristan Taormino's crazy-helpful Ultimate Guide to Anal Sex for Women, she mentions that Crisco has been a favorite of the LGBT community for a long time, but it's bad to use with condoms because it can eventually poke tiny holes in the latex.

The oil-based ones are also pretty annoying to get off afterwards. We used Vaseline, but my boyfriend later realized that it deadens sensation on the skin, which was obviously helpful for my asshole but bad for his orgasm. So maybe don't do that, or start with a bit of that but then switch, because it'll take really long for your partner to come, if they even can.

5. Getting the tip in hurts the most, because the head of the penis is the widest part. Once you're past that and up to the shaft, it'll feel a little better. Remember how much regular sex hurt at first, for some of us? (Unless I guess the guy's shaft is the same width as his head, in which case are you guys gonna break up when he has to go back to Xavier's Academy for Gifted Youngsters?)

6. Relax your PC muscles as much as possible. Relaxing and constricting the pubococcygeus (PC) muscles is like the anal version of doing Kegels. You can worry about that later on — right now just let your butthole muscles go, like you're about to poop (you won't, probably).

7. You're going to freak the fuck out that you're pooping but you're not. Honestly, it becomes hard to tell if you are or aren't; additionally, this Tucker Max story was not helpful for my butt sex-phobia. You're probably not gonna poop. If there's a little bit of poop, as my partner said, it's not a big deal, because "[he] asked for this." (There wasn't.)

8. You can lie flat on your stomach, get in doggy-style, or do missionary — and that is the order of what will hurt the least to the most. At least, in my (minimal) experience. You can tear your anus if you use a certain position that allows for more penetration before you're ready, and Taormino points out that the missionary position allows for the least clitoral stimulation and suggests receiver-on-top for beginners. "Insertive partners who are inexperienced, nervous about how to penetrate their partners anally, or fearful of hurting their partners may find this position most relaxing because the receiver can do much of the decision-making and work."

Don't worry about disappointing him by wanting to go slow and gently. You're not being a buzzkill who's squashing his porn-influenced fantasies of pounding the shit out of a girl's butt. You are being an awesome and selfless (if butt sex is not on your list of must-have sex) partner.

9. Like peeing immediately after sex to avoid a UTI, it's good to go to the bathroom right after you're done. You'll also probably feel like you have to anyway. You have also opened yourself up to the joy of butt queefs. They're not farts, no matter what anyone says. Unlike frontal queefs, they might go on for a few hours as the air escapes. On the bright side, you are a human beatbox, and your partner can lay a sick freestyle over the top if s/he feels so inclined.

10. If you despise it, never do it again. It shouldn't take you a few hellish rounds to finally decide it's not for you. If you hate it, you hate it, and that is fine. I didn't hate it, and it was psychologically gratifying to watch my partner's mind being blown. I'd do it again as a "special occasion" thing, like on our anniversary, or Flag Day.